Tetrahydrofuran → 4-(2-oxo-4-(pyridin-4-yl)imidazolidin-1-yl)-N-((R)-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)piperidine-1-carboxamide

HRID 1867616ノート

反応式

HRID 1867616 の反応式
[NH2:1][C@@H:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:3]1=[O:24].C(N(CC)CC)C.[NH:32]1[CH2:37][CH2:36][CH:35]([N:38]2[CH2:42][CH:41]([C:43]3[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=3)[NH:40][C:39]2=[O:49])[CH2:34][CH2:33]1.[O:50]1CCC[CH2:51]1>>[O:24]=[C:3]1[C@H:2]([NH:1][C:51]([N:32]2[CH2:33][CH2:34][CH:35]([N:38]3[CH2:42][CH:41]([C:43]4[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=4)[NH:40][C:39]3=[O:49])[CH2:36][CH2:37]2)=[O:50])[N:8]=[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]1[CH2:19][C:20]([F:21])([F:23])[F:22]

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 8471Triethylamine2 回HCID 10854086HCID 10854086、化合物HCID 579795681-Piperidin-4-yl-4-pyridin-4-ylimidazolidin-2-one

生成物 1

HCID 115272874-(2-oxo-4-(pyridin-4-yl)imidazolidin-1-yl)-N-((R)-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)piperidine-1-carboxamide

実験手順

(3R)-3-Amino-5-phenyl-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (49 mg, 0.146 mmol) (Y.-J. Shi et al., Tetrahedron, 1999, 55, 909-918) and triethylamine (0.020 mL, 0.146 mmol) were added to a solution of p-nitrophenylchloroformate (29 mg, 0.146 mmol) in tetrahydrofuran (5 mL) at 0 oC. After 1 h, 1-piperidin-4-yl-4-pyridin-4-ylimidazolidin-2-one (36 mg, 0.146 mmol) and additional triethylamine (0.040 mL, 0.292 mmol) were added and the reaction warmed to ambient temperature. After 16 h, the reaction was concentrated and partitioned between dichloromethane and saturated sodium bicarbonate. The organics were washed with water, brine, and dried over magnesium sulfate. Purification by silica gel chromatography (100% dichloromethane→15% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (36 mg). MS 606.2 (M+1)

後処理

  1. waitAfter 16 h
  2. concentrationthe reaction was concentrated
  3. custompartitioned between dichloromethane and saturated sodium bicarbonate
  4. washThe organics were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customPurification by silica gel chromatography (100% dichloromethane→15% methanol {1% ammonium hydroxide}/dichloromethane)

出典と根拠

ORDレコード
ord-720d78a52e394d37803074abdea2d8db
出典データセット
uspto-grants-2009_12
特許番号
US07632832B2

反応ノート

読み込み中…